It’s Valentine’s Day, and Jackie Hoffman is onstage at Joe’s Pub, the East Village cabaret space, giving “the gift of hatred for the day of love.” Never mind that the New York Times called Jackie Five-Oh!, her sixth original one-woman show, “savagely funny,” or that The Addams Family, the Broadway musical in which she plays the cackling, scene-stealing grandma, is a commercial hit. Hoffman is the theater world’s consummate complainer, with a gift for, as she puts it, “making lemons out of lemons.” Whether she is mining her Orthodox upbringing or settling professional scores, Hoffman lets no potential grievance go to waste. As she sang in a previous solo engagement, The Kvetching Continues:

Fuck the silver lining! I’ll always find a cloud.
Not only will I find one, I’ll criticize it loud.
If you say my hair looks nice, you don’t like my ass.
Not only is it half empty—I don’t have a glass.

It’s an accurate description of how Hoffman moves through life. Mention that Jackie Five-Oh!­­—a celebration of her “first fiftieth birthday”—has just been extended a second time (it plays tonight and on April 4), and she’ll gripe that the extra performances mean “more time to be paranoid because I’m always sick.”

How does she feel about turning 50? “It may settle in when I finally have that colonoscopy, which I don’t have time to do.” (A recurring segment in her act is called “What Was I Diagnosed With This Year?”)

As for The Addams Family, Hoffman spends much of Jackie Five-Oh! enthusiastically tearing it down. After getting blasted with across-the-board pans, the musical became, in her words, “the most reviled, criticized, loathed, victimized, shat-upon, financially successful group of people since the Jews.” At Joe’s Pub, she quotes some of the critics’ meanest zingers, including a paraphrase from USA Today: “As Grandma, Jackie Hoffman is hunched over, screeching, and just downright irritating.” Hoffman hurls the line back like a stink bomb.

To make matters worse, she doesn’t get to screech enough. “Every character in The Addams Family has a song but Grandma,” she groans. “Lurch has a song. Fucker doesn’t even talk!” During rehearsals for The Addams Family, Hoffman wrote her own solo number for Grandma, which she submitted to the creative team; having yet to receive a green light, she debuts the song in her Joe’s Pub show. (The director Jerry Zaks, who worked on The Addams Family, explains, “It’s a wonderful song, but I don’t know that it would fit the story moving forward.”)

The reviews for Jackie Five-Oh! have inevitably, if admiringly, described Hoffman as biting the Broadway hand that feeds her. But Hoffman has always used her solo act as a counterweight to professional disappointment—or even success. During her Broadway debut, in Hairspray, in which she played a trio of bit parts, she spent her off nights performing The Kvetching Continues, which included an ode to underutilization called “Three Minutes on Broadway.” In Jackie Five-Oh!, she devotes an entire song to the fact that she was replaced in a movie by Queen Latifah, thus depriving her of health benefits from the Screen Actors Guild:

I have asthma, can’t afford my inhaler.
I will drown in mucus, groping for breath.
When you read my obituary in the paper,
Queen Latifah will be my cause of death!

To her downtown fans, Hoffman is a perpetually wronged diva, an irrepressible underdog who has been denied her due. With her “old Semite face” and cranky demeanor, she’s what casting agents euphemistically call “specific.” But resentment only gives her fodder. As she tells the Joe’s Pub crowd, “I would have won a Tony if there were a category called Hating Other People’s Careers While Combining Maker’s Mark, Ambien, and Pinkberry.”

One day, Hoffman arrives for a late lunch after an Addams Family matinee. She is suffering from some “fakakta flu,” which she picked up on the plane back from Disney World with her husband, the jazz trumpeter Steve Smyth. Given her professed distaste for children (“You won’t see me lactatin’, / There’s no child that’s not worth hatin’ ”), the destination comes as a surprise.

“Baghdad would be more likely,” she concedes. “I’m a child hater and I went to Disney World. Where they force you to be happy. And they wave a lot. They like waving.” How did she endure the stroller crowd? “I had to adopt a kind of a Zen attitude,” she says, not quite convincingly.

Reflecting on her childhood in Bayside, Queens, Hoffman imagines that she was no less bratty than the Epcot set. “I was probably a loud shrew: spoiled, demanding,” she says. The youngest of four children by eight years, Hoffman craved attention. At age 5, she would tramp around the house singing Frank Sinatra’s “You Make Me Feel So Young,” uncertain why she was getting a laugh.

Hoffman’s mother was raised Orthodox, unlike her father, who never got the hang of kosher living. “He’d run around on Friday nights screaming, ‘This is fucking voodoo! I have to pay the Long Island Lighting Company and we’re turning lights off?’ ” She counts her father among her early comedic heroes. (The others are Carol Burnett, the Marx Brothers, Dick Van Dyke, and Bugs Bunny.) An advertising art director and amateur pianist, he was “Gleason-like,” Hoffman recalls. “Really high-strung, gravel-voiced. Extremely funny. He got into acting later in his life and would do community theater.” Hoffman’s parents exposed her to live performance early on: She saw Steve and Eydie at the Westbury Music Fair, No, No, Nanette on Broadway. “By the time I was a 9-year-old girl I was a gay man,” she says.

Jewishness was central to Hoffman’s pull toward comedy. “Anywhere there’s misery is funny,” she says. For a while, she embraced the family fervor. She joined the Orthodox-affiliated National Conference of Synagogue Youth (“the happiest time in my mother’s life”) and spent five years at yeshiva before begging her parents to let her loose. As it turned out, public high school in Great Neck—“the J.A.P. capital of the world”—was no better. Hoffman was pudgy, sheltered, and despised. She started acting in school plays to avoid taunting.

By the time she was 21, Hoffman was self-possessed enough to land her first professional gig, playing Plain Jane Wayne, the Terror of the Plains, in Shootout at the Trailblazer Saloon, a kiddie show at Hershey Park, in Pennsylvania. “I had a song in that one,” she observes. “I was the star! That was the last time.”

Hoffman moved to New York to pursue acting, but a temp job at a ticket agency turned full-time, and she was getting nowhere. Then a co-worker—“a married guy I was fucking for years”—suggested that she audition for Second City, the star-making Chicago improv group. She flew out to audition and, in 1987, began a seven-year stint.

Hoffman’s contemporaries at Second City—though she is loath to play the “who’s more famous than you” game—included Steven Colbert, Steve Carrell, and Amy Sedaris, who was working as a cocktail waitress when she met Hoffman. “I liked her look,” Sedaris recalls of their first encounter. “She had this dress on with pants underneath and big glasses. My eye went right to her.”

Sedaris remembers Hoffman as a gifted improviser whose comedic skills hearkened back to a lost vaudevillian age. In the mid-nineties, Sedaris moved to New York to write plays with her brother David, billing themselves The Talent Family. Hoffman joined them soon after, and in 1995 she co-starred in their satirical pastiche One Woman Shoe at a tiny downtown theater, for which she also wrote the theme song. Two years later, in The Talent Family’s Incident at Cobbler’s Knob—a cracked fable about woodland creatures—Hoffman played a squirrel. (The Times called her “a treasure.”)

As the Sedaris siblings rose to fame, their theatrical projects gave Hoffman a professional boost. Her final collaboration with them was The Book of Liz, in 2001, in which she played multiple supporting roles to Amy’s title character, a questing member of an Amish-like sect called the Squeamish. Amy recalls, “We had this scene where she was a doctor, and we had to play it pretty straight—but we cracked up every night. Being with her onstage, it’s hard not to laugh.” For her performance, Hoffman won an Obie, the award for Off Broadway theater.

Around the same time, she got involved with Tweed, a gay-centric theater company that was home to such pioneering drag artists as Charles Busch and John Epperson. Under its aegis, Hoffman performed a solo act, Jackie’s Kosher Khristmas, and starred in bitchy reenactments of old classics like The Children’s Hour and Imitation of Life.

Hoffman credits Tweed with introducing her to a gay audience, which in turn exposed her to “gay men with power.” It was members of this subset who enabled her leap to Broadway: Marc Shaiman and Scott Wittman, who wrote the score of Hairspray, and Douglas Carter Beane, the book writer of Xanadu, who wrote the part of the evil muse Calliope especially for her. In the latter, the Times critic Charles Isherwood described Hoffman as “a Roz Chast cartoon sprung to life.”

Jackie Hoffman and Adam Riegler in The Addams Family.Joan Marcus

Do not be deceived by this apparent rise to success. As Hoffman is quick to point out, “The list of people who said ‘no’ is astounding.” Over a plate of Chilean sea bass, she catalogs all the Broadway roles she didn’t get: Domina in A Funny thing Happened on the Way to theForum, Jonesy in How to Succeed in Business Without Really Trying, “Mrs. Whatever-the-Fuck” in The Importance of Being Earnest.

“I had a great audition—but did not get to replace Andrea Martin in Young Frankenstein,” she says, referring to the Mel Brooks musical from a few years back. Even now, with three Broadway credits to her name, Hoffman anticipates—even revels in—the rejection to come. “I’m campaigning for Miss Hannigan in Annie in 2012,” she says, “but I know I won’t get it.”

Although she has had memorable roles in films, including Kissing Jessica Stein and Garden State, she insists that Hollywood has no place for her, even when wacky-sidekick roles come up. Amy Sedaris recalls getting cast as the nosy neighbor Gladys Kravitz in the Bewitched movie and feeling pangs of guilt, even though Hoffman hadn’t auditioned. “I said, ‘Oh, you gotta cast Jackie Hoffman instead! Here’s her number!’ ”

Hoffman blames the industry’s antipathy toward older women. “Youth has taken over in such an aggressive way,” she says. “And now that movie stars have a hankering to do theater, it does appear hopeless. But I keep plugging because I don’t know how to do anything else.”

Speaking of indignities, how about the one where the producers of Xanadu, in an attempt to goose ticket sales, replaced her with Whoopi Goldberg for six weeks in the middle of the run? “I was crestfallen,” Hoffman says. (Between that and Queen Latifah, she acknowledges that she has a strange history of getting replaced by black women.)

To make matters worse, the furlough coincided with her wedding. “The theme was ‘Xan-I-Do’ ” she says. “Get it? All the little postcards and the signs said ‘Xan-I-Do.’ And when the producer, who was 20, sat me down and told me I was going to be out, the first thing I said was, ‘But my wedding’s called “Xan-i-Do!” ’ ”

Still, it’s hard to imagine any slight or impediment that wouldn’t end up fueling her comic engine. In 2006, while appearing in the Paul Rudnick play Regrets Only, Hoffman discovered a benign tumor and had to undergo a hysterectomy. Months later, she was rehashing the ordeal in her one-woman show Jackie With a Z—the title is a riff on Liza Minnelli’s Liza With a Z—which featured a duet between Hoffman and a puppet version of her uterus. (Uterus: “You can’t get rid of me that easy.”)

In Jackie Five-Oh! her complaints are less dire: a fruitless audition for Men in Black III, a Dominican vacation that got spoiled by the Haitian earthquake. In one winning sequence, she reenacts a recent trip to the Bagel Mentch, in Great Neck, while visiting her mother:

Old Jewish Man: I understand you’re working as a professional?
Jackie’s Mom: She’s in a play! She’s in a play!
Shrieking Jewish Lady: Is she famous? My granddaughter just asked. Is she famous? Get her autograph? If she’s famous. What play are you in?
Jackie: The Addams Family.
Shrieking Jewish Lady: Alright, we won’t get the autograph. We’ll go.

Later on, she sings a gloriously tasteless number bemoaning the fact that she hasn’t been cast in a Holocaust movie. (At least one offended audience member has written in to complain.) As the raucous applause subsides, Hoffman stops and stares at a guy in the front row. “Are you Clinton Kelly from What Not to Wear?”

“I am,” the guy says.

“I love your show!” Hoffman squeals. As she moves on to her next bit, the crowd seems distracted. Some of them crane their necks to catch a glimpse of Kelly. “What’s happening now? Did I kill my own 15 minutes?” Hoffman says, looking thrown. Then she turns back to Kelly and tells him: “Your show sucks.”

* * *

On a Wednesday afternoon, Hoffman enters the stage door of The Addams Family. Minutes after arriving in her dressing room, the kvetching begins. “Shows you what priority I have around here,” she grumbles, as the wig supervisor, Barry Ernst, enters panting, explaining that he has been detained by Bebe Neuwirth, who plays Morticia.

In his absence, Hoffman has begun her transformation, donning a hairnet, applying a corpse-colored base, and drawing thick age lines to accentuate her wrinkles. “Age, age, age,” she says to the mirror.

Still catching his breath, Ernst dabs her forehead with a thin liquid adhesive and pastes on two gnarled granny eyebrows. As he works, the two catch up on Charlie Sheen’s 20/20 interview.

Ernst affixes two hideous fake moles to Hoffman’s nose and chin. “They’re made out of silicone,” he explains. Finally, he applies her wig—a tangled gray mop that engulfs Hoffman’s head like a wild sloth.

“Thanks, bubeleh,” Hoffman says.

A dresser arrives and fits Hoffman into baggy pink bloomers, an itchy-looking brown dress, and a floral shawl straight out of Satan’s thrift store. “Thanks, mamala,” Hoffman tells her. Then she spins around, and a frightful 102-year-old deadpans, “The rest of the magic is done by a wacky voice and a lot of faces and lip-smacking.”

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